Acetic Acid → HCID 57014251, compound

Participants

Reaction Steps

A solution of (1R,2S,4R)-2-benzyloxy-5-ethyl-4-methoxy-6,8-dioxabicyclo[3.2.1]octane (see Example 15.2) (3.4 g) in absolute ethanol (150 ml) containing acetic acid (2 ml) and 5% palladium on barium sulphate (1 g) was shaken in a hydrogen atmosphere at 40 p.s.i for 24 h, and then the solution was filtered and the solvent was removed. Chromatography of the residue on silica gel gave the title alcohol; m.p. 52°-53° C.; [α]D -97.1°; 13C nmr data: 108.2 (C-5), 78.7 and 78.0 (C-1 and C-4), 66.9 (C-2), 66.3 (C-7), 57.6 (OCH3), 27.0 and 26.0 (C-3 and CH2CH3), and 6.4 (CH2CH3).

Provenance & Evidence